Casual Dresses

Explore the array of casual dresses perfect for brunch with your besties to stroll around the farmers market on the weekends. Discover a variety of casual fabrics like ribbed knit, denim, mesh, linen, or cotton gauze. Browse the variety of skater dresses, sundresses, t-shirt dresses, and boho-inspired maxis. Look out for off-the-shoulder mini dresses, tropical print shift dresses, and tie-dye ribbed dresses perfect for a laid-back vibe but always with a chic aesthetic.

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CASUAL DRESSES
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STYLE SPOTLIGHT

Cute Work Dresses

Women's Boots & Booties

Floral Print Dresses

Everyday Casual Dresses That Are Essential For Fall

It's time to elevate your look with cozy and stylish casual dresses from Windsor. Whether you're planning a leaf-peeping trip, catching up with friends over a warm latte, or simply looking to refresh your fall closet, our selection of trendy casual dresses for women has you covered.

For fall 2024, embrace rich autumnal colors like deep burgundy, burnt orange, or olive green. These shades perfectly capture the cozy essence of the season. Opt for casual dresses made from comfortable fabrics like rib knit, jersey, or faux suede to keep you warm as the weather cools. If you prefer an effortlessly chic look, try a sweater dress. This versatile style is ideal for transitioning from a casual day out to a cozy evening gathering. Pair it with ankle boots, a wide-brim hat, and a faux leather jacket for an on-trend fall look.

Looking for a dress that effortlessly takes you from day to night? Consider our selection of casually chic sweater dresses. These styles are polished yet cozy, perfect for any occasion. Elevate your casual dress ensemble with a pair of knee-high boots and a statement scarf for a sophisticated fall outfit.

Long casual dresses are also a must-have for fall 2024. Opt for casual maxi dresses in smooth, contouring designs made from lightweight fabrics. Choose from earthy tones like taupe and chocolate brown or go for classic black for the most versatile look. Wear your long casual dress with a chunky cardigan, leather sneakers, and a crossbody bag for a flawless #OOTD.

Whether you're planning a holiday getaway or simply updating your wardrobe, a smart casual dress code is an essential addition. They're comfortable, versatile, and perfect for any occasion. Refresh your closet with elevated casual dresses from Windsor and stay on-trend this fall. Shop now online or in-store!

What Makes A Dress Casual?

Aside from special occasion dresses and gowns, dresses can be casual depending on how you style them. Fabrication and design can also innately make a dress casual so choose knits and cotton blends or ditsy florals or neutral tone prints, like a snake print dress, as everyday basics. Knit and sweater dresses, updated regularly here, are stylish choices for work or date night. Avoiding heels and heeled mules, and pairing sneakers and lug boots instead come in handy to make any dress look more laid back. Layering knits like cardigans, sweaters, or even classic jean jackets that are naturally casual over any dress is an easy way to instantly dress down the look. Casual dresses with drawstrings and tie or button fronts are details that can give those laid-back vibes too. Like with shoes, often it’s what you wear with the dress that “dresses down” your look so choose hair accessories, makeup, and jewelry accordingly.

How Do I Style A Dress Casually?

Style a dress casually by choosing to complement apparel and accessories that are naturally casual like jean jackets, t-shirts, scrunchies, dainty or basic jewelry, simple crossbody bags, and casual shoes like strappy sandals or combat boots. Take a ruched form-hugging mini dress and add on a simple lariat necklace and chunky sneakers for a cool and casual look. Layer on a denim jacket over a basic knit midi dress and pair it with slides for a casual-chic feel. For road trips or weekend getaways, maxi and midi dresses can be layered any time of year with graphic tees and sandals or cropped sweaters and combat boots to create that laid-back vibe. Windsor has the best-selling selection of women's casual dresses and accessories to pair them with for that must-have chill look. Need some help? Our in-store stylists are always ready to help you find your perfect outfit. Come shop with us!

  • Pleasant Cutie Collared V-Neck Belted Midi Dress

    Make your look sweet and simple in this sleeveless midi dress perfect for summer plans! The collared V-neckline and button-down closures offer a classic touch, while the adjustable belted waist gives you a flattering A-line silhouette complete with a midi-length hem. Style this midi dress with wedges and earrings.

    Fit & Features

    • Woven fabric with lining, no stretch
    • Collared V-neckline
    • Button-down closures
    • Adjustable belted waist with buckle
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3347

    Category Name: Casual Dresses

    Price: $9.97 $59.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK, TAUPE

    Available Size: S, M, L

    Product Badge:
    • Sale
  • Best Spot To Be Off-The-Shoulder Polka Dot Mini Dress

    Wherever you are in this off-the-shoulder polka dot mini dress is the best spot to be! The ruffled neckline with non-slip grip lining adds a flirty touch while the stretchy smocked bodycon silhouette highlights your curves. The tiered ruffle mini-length hem and polka print add a playful and chic vibe to this woven dress. Complete the look with earrings and cute booties!

    Fit & Features

    • Polka dot print, lined woven fabric
    • Ruffled off-the-shoulder neckline
    • Stretchy smocked bodycon silhouette
    • Ruffled mini-length hem
    • Runs true to size

    Style Number/Barcode: 05102-5553

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Sweet Looking Long Sleeve Denim Mini Dress

    A denim mini dress features long sleeves, a classic collar neckline, flap pockets for style, and a flattering bodycon silhouette. Perfect for back-to-school and styling with sneakers or boots.

    Fit & Features

    • Denim fabric, minimal stretch
    • Long sleeves with button cuffs
    • Collar neckline
    • Front zipper closure
    • Flap pockets
    • Bodycon mini-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5448

    Category Name: Casual Dresses

    Price: $35.00 $49.90

    On Sale: Yes

    Availability: In Stock

    Available Color: DENIM

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Favorite Fleur V-Neck Floral Chiffon Skater Dress

    Give them a twirl in this adorable floral chiffon skater dress at birthdays or graduation parties! Featuring puff short sleeves, a tie front bust, and a stretch smocked empire waist, this dress will hug your curves in all the right places. The skater silhouette and ruffled hem add a playful touch to this flowy chiffon dress. Complete the look with teardrop earrings.

    Fit & Features

    • Floral print, chiffon fabric lined with stretchy knit
    • V-Neckline, tie front
    • Skater silhouette
    • Ruffled hem
    • Runs true to size

    Style Number/Barcode: 05101-3135

    Category Name: Casual Dresses

    Price: $6.97 $44.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S

    Product Badge:
    • Sale
  • Think About Me Lace-Up Floral Skater Dress

    Captivate everyone's thoughts in this floral skater dress sure to be the prettiest pick anyone has ever seen! With a square neckline and spaghetti straps, it's perfect for warmer days. The lace-up back and bow tie adds a playful touch, while the skater silhouette and mini-length hem flatter any figure. Complete the look with an adorable hair bow and sunglasses!

    Fit & Features

    • Floral print, woven fabric lined, no stretch
    • Spaghetti straps
    • Square neckline, bow tie
    • Lace-up back
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5490

    Category Name: Casual Dresses

    Price: $6.97 $42.90

    On Sale: Yes

    Availability: In Stock

    Available Color: GREEN

    Available Size: XS, S

    Product Badge:
    • Sale
  • Whimsical Beauty Strappy Back Textured Knit Skater Dress

    Radiate whimsical beauty in this gorgeous textured knit skater dress perfect for graduations or parties! The sheer textured knit fabric includes a full-length knit lining and offers plenty of stretch. The dress is shaped with a sleeveless square neckline and dual spaghetti straps leading to a bold open back with a cross-back strappy design. The high waist flows out to a short skater skirt with an adorable fit and flare silhouette. Style with hoop earrings and espadrille sandals.

    Fit & Features

    • Sheer textured knit fabric, full-length knit lining
    • Plenty of stretch
    • Square neckline, dual spaghetti straps
    • Open back, cross-back strappy design
    • High waist, short skater skirt
    • Fit and flare silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3142

    Category Name: Casual Dresses

    Price: $9.97 $46.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Special Stunner One-Shoulder Cutout Ombre Maxi Dress

    Leave everyone in awe when you're in this ombre maxi dress for sunset cocktails! Featuring a unique one-shoulder neckline with an adjustable spaghetti strap and flirty side cutout, this dress hugs your curves and shows off your legs with a high-side slit along the maxi-length hem and form-hugging silhouette. Complete the look with sparkly bracelets.

    Fit & Features

    • Ombre mesh fabric, stretchy knit lining
    • One-shoulder neckline, adjustable spaghetti strap
    • Side cutout
    • High side slit
    • Form-hugging, maxi-length silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5709

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: In Stock

    Available Color: MAGENTA

    Available Size: XS

    Product Badge:
    • Sale
  • Romance That Wows Large Blossom Floral Maxi Dress

    Make a stunning entrance in this large blossom floral maxi dress at dinner while on vacation or the weekend! Showcasing a statement blossoming floral print, this maxi dress is designed to turn heads. With a flattering V-neckline and delicate spaghetti straps, this dress hugs your curves in a bodycon silhouette and is finished with a maxi-length hem. Complete the look in strappy sandals and earrings!

    Fit & Features

    • Large blossoming floral print
    • Mesh fabric lined with stretchy knit
    • Spaghetti straps
    • Bodycon silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3343

    Category Name: Casual Dresses

    Price: $45.90

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Pretty In Plaid Drop Waist A-Line Mini Dress

    Fit & Features

    • Plaid-printed linen-blend woven fabric with woven lining, no stretch
    • Plunge V-neckline
    • Tie-back halter straps
    • Partially open back, hidden zipper with hook-eye closure
    • Drop waist
    • Mini-length pleated A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5852

    Category Name: Casual Dresses

    Price: $28.00 $39.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BROWN

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Artsy Flair Strapless Cutout Abstract Mini Dress

    Showcase an artsy flair in this abstract mesh mini dress tonight! Featuring a striking strapless neckline, side ruched seams for a flattering fit, and a unique side cutout design, this bodycon mini-length dress is all about highlighting your curvaceous figure. Complete the look with stiletto heels.

    Fit & Features

    • Abstract print, mesh fabric, stretchy knit lining
    • Strapless neckline
    • Side cutout
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5693

    Category Name: Casual Dresses

    Price: $9.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Garden Of Roses Chiffon Midi Dress

    Frolic through the garden or your next soiree in this rose print chiffon midi dress! It features a sleeveless sweetheart neck, spaghetti straps, a ruched bust with a tie, and a slim A-line silhouette with a flirty front slit. Complete the look in strappy block heels.

    Fit & Features

    • Sleeveless sweetheart neck, spaghetti straps
    • Ruched bust with tie
    • Back zipper and hook-eye closure
    • Slim A-line silhouette
    • Front slit, midi-length hem
    • Rose print, airy chiffon fabric, stretch knit lining
    • Runs true to size

    Style Number/Barcode: 05101-2081

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Tempting Allure Sweetheart A-Line Lace Mini Dress

    A lace A-line mini dress that will captivate everyone in the room! With a playful sweetheart neckline, adjustable spaghetti straps, and an underwire bust, this dress accentuates your curves, while the A-line silhouette and ruffled tie mini-length hem add a touch of whimsy. Complete the look with a clutch for a dressy evening event.

    Fit & Features

    • Lace fabric lined with stretchy knit
    • Sweetheart neckline, adjustable tie
    • Adjustable spaghetti straps
    • Underwire bust, back zipper and hook-eye closure
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3300

    Category Name: Casual Dresses

    Price: $9.97 $44.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: M

    Product Badge:
    • Sale
  • Ahead Of The Curve Crew Neck Bodycon Mini Dress

    A sleeveless mini dress that's ahead of the curve in every way! With a flattering bodycon fit and a mini-length hem, this dress will accentuate your curves in all the right places. The crew neckline and side ruched seam add unique details to this stylish dress. Complete the look with a crop jacket and sandals for any plans!

    Fit & Features

    • Slinky knit fabric lined with stretchy knit
    • Crew neckline
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5753

    Category Name: Casual Dresses

    Price: $23.00 $32.90

    On Sale: Yes

    Availability: In Stock

    Available Color: WHITE

    Available Size: XS, M

    Product Badge:
    • Sale
  • Bold New Look Corset Lace-Up Linen Skater Dress

    Make a bold impression in this corset linen skater dress all season long! The sweetheart neckline with a bust tie and adjustable straps provides a flattering fit while the flexible boning supports your shape. The strappy lace-up back adds a touch of playfulness to the skater silhouette and short-length hem. Complete the look in wedge sandals and a handbag.

    Fit & Features

    • Linen blend fabric lined with stretchy knit
    • Sweetheart neckline with bust tie
    • Adjustable straps, side zipper and hook-eye closure
    • Strappy lace-up back
    • Flexible boning
    • Skater silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3256

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: In Stock

    Available Color: NATURAL

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • More Than Sweet Tie Strap Fit-And-Flare Dress

    Who can imagine a look sweeter than this fit-and-flare dress? Showcase your darling side in this short eyelet dress at casual brunches or parties! This charming dress features a square neckline, tie shoulder straps, and a flattering fit-and-flare silhouette. With a tiered ruffled short-length hem and delicate eyelet lace fabric, this dress will have you looking and feeling your best. Complete the look in trendy sneakers for a cute style!

    Fit & Features

    • Sheer eyelet lace fabric with knit lining, moderate stretch
    • Square neckline
    • Tie shoulder straps
    • Fit-and-flare silhouette
    • Tiered ruffles
    • Runs true to size

    Style Number/Barcode: 05102-5532

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • So Enchanting A-Line Floral Chiffon Midi Dress

    Have everyone under your spell in this floral chiffon midi dress as a stunning wedding guest or to attend a garden party! Featuring a square neckline with a bust tie, elasticized shoulder straps, and an A-line silhouette, this dress flatters any figure. The front slit and midi-length hem add a touch of sophistication. Complete the look in block heels and earrings!

    Fit & Features

    • Floral print, chiffon fabric, stretchy knit lining
    • Elasticized shoulder straps
    • Square neckline, bust tie
    • Back zipper and hook-eye closure
    • Front slit
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05101-3304

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Leave An Impression Twist Cutout Knit Midi Dress

    Leaving an impression will be easy with this sleeveless knit midi dress! Perfect for vacation or a weekend spent at the beach, this dress features a flattering scoop neckline, spaghetti straps, a head-turning twist cutout back design, a bodycon fit, and a sultry side slit along the midi-length hem. Complete the look in strappy espadrille wedges.

    Fit & Features

    • Knit fabric, moderate stretch
    • Scoop neckline
    • Spaghetti straps
    • Twist back cutout
    • Side slit
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 06005-1950

    Category Name: Casual Dresses

    Price: $36.90

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Boho Lace Off-The-Shoulder Drop Waist Romper

    Fit & Features

    • Sheer lace fabric with knit lining, moderate stretch
    • Off-the-shoulder straight neckline, ruffled overlay
    • V-shaped drop waist
    • Flowy shorts, skater silhouette
    • Romper in size small is 25" shoulder to hem with an 8.5" front rise and a 3" inseam
    • Runs true to size

    Style Number/Barcode: 06503-1228

    Category Name: Casual Dresses

    Price: $32.00 $39.90

    On Sale: Yes

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

    Product Badge:
    • Sale
  • Looking Back Strapless Strappy Mini Dress

    Make everyone look back at you in this sassy rib knit mini dress! Perfect for summer BBQs or pool parties, this dress boasts a flattering strapless neckline and bust cutout, a strappy back design, and a bodycon fit. Complete the look in sandals and sunnies!

    Fit & Features

    • Rib knit fabric, sewn-in knit lining, moderate stretch
    • Strapless neckline
    • Strappy back
    • Bodycon fit
    • Runs true to size

    Style Number/Barcode: 05102-5767

    Category Name: Casual Dresses

    Price: $9.97 $34.90

    On Sale: Yes

    Availability: In Stock

    Available Color: LIME, ROYAL

    Available Size: M, L

    Product Badge:
    • Sale
  • Signature Stripes Strapless A-Line Maxi Dress

    Show off your signature style in this striped maxi dress perfect for casual summer plans! Features a strapless neckline, a stretchy smocked bodice for a comfortable fit, and a flattering A-line midi silhouette with hidden side pockets to keep your hands warm. Complete the look with sunglasses and trendy sandals.

    Fit & Features

    • Striped pattern, cotton woven fabric, no stretch
    • Strapless neckline
    • Stretchy smocked bodice
    • Hidden side pockets
    • A-line midi silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5802

    Category Name: Casual Dresses

    Price: $9.97 $52.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLUE

    Available Size: L

    Product Badge:
    • Sale
  • Cute Feels Off-The-Shoulder Sweater Mini Dress

    Feel cute in this off-the-shoulder sweater mini dress all year round! The folded off-the-shoulder neckline adds a flirty touch, while the bodycon fit accentuates your curves perfect for a day or night on the town. Complete the look in block heels.

    Fit & Features

    • Sweater knit fabric, moderate stretch
    • Off-the-shoulder neckline
    • Bodycon fit
    • Mini-length
    • Runs true to size

    Style Number/Barcode: 06005-1947

    Category Name: Casual Dresses

    Price: $17.97 $42.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Here Comes The Sun Strapless Ruffle Mini Dress

    Here comes the sun and you radiating sunshine in this strapless mini dress perfect for casual plans! Featuring a flattering strapless neckline, side ruched seams, and a bodycon fit, this dress will hug your curves in all the right places. The ruffled mini-length hem adds a playful touch! Complete the look in sandals and sunnies!

    Fit & Features

    • Brushed knit double-lined fabric, moderate stretch
    • Strapless neckline
    • Bodycon fit
    • Ruffled hem
    • Runs true to size

    Style Number/Barcode: 05102-5843

    Category Name: Casual Dresses

    Price: $9.97 $32.90

    On Sale: Yes

    Availability: In Stock

    Available Color: SAGE

    Available Size: M, L

    Product Badge:
    • Sale
  • Charming Allure Tie-Front Ruffled Skater Dress

    Captivate with your charming allure in this pretty tie-front ruffled skater dress! Designed with a breezy gauze woven fabric, this short dress is the perfect lightweight style for weekend dates. It features a sleeveless V-neckline with the cutest tie-front bow design, a built-in padded bust, adjustable spaghetti straps so you can find your perfect fit, and a smocked back for added stretch. The high waist flows out to a tiered ruffled skater skirt with an adorable fit-and-flare silhouette. Complete your look with hoop earrings and heeled sandals.

    Fit & Features

    • Gauze woven fabric with woven lining, no stretch
    • V-neckline with tie-front, padded bust
    • Adjustable spaghetti straps
    • High waist, smocked back
    • Tiered ruffled design
    • Fit-and-flare skater silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5720

    Category Name: Casual Dresses

    Price: $9.97 $49.90

    On Sale: Yes

    Availability: In Stock

    Available Color: OLIVE, BLACK-2

    Available Size: S, M, XS, L

    Product Badge:
    • Sale
  • Must-Have Tie Back A-Line Mini Dress

    A must-have tie back A-line mini dress for casual nights out! Featuring chic cap sleeves, a square neckline, a sultry open back with tie closure, and a flattering A-line silhouette with a mini-length hem, this dress will elevate your style game. Complete the look in faux suede heels and a purse!

    Fit & Features

    • Slinky knit fabric lined with stretchy knit
    • Open tie-back design
    • A-line silhouette
    • Runs true to size

    Style Number/Barcode: 05102-5681

    Category Name: Casual Dresses

    Price: $22.00 $30.90

    On Sale: Yes

    Availability: In Stock

    Available Color: BLACK

    Available Size: XS, S, M, L

    Product Badge:
    • Sale